Received 23 March 2009
aDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Nám. T. G. Masaryka 275, Zlín,762 72, Czech Republic, and bDepartment of Chemistry, Faculty of Science, Masaryk University in Brno, Kamenice 5, Brno-Bohunice, 625 00, Czech Republic
Correspondence e-mail: email@example.com
In the racemic crystal of the title compound, C17H23NO, enantiomers of the two crystallographically independent molecules are linked into face-to-face RSdimers via intermolecular O-HN hydrogen bonds and - interactions with centroid-centroid distances of 3.7610 (2) Å. The molecules adopt slightly different conformations and contain an adamantane cage consisting of three fused cyclohexane rings in almost ideal chair conformations, with C-C-C angles varying within the range 107.2 (4)-111.4 (4)°. In the hydrogen-bonded pair, the benzene rings are almost coplanar, the dihedral angle between them being 1.29 (13)°. The molecular packing in the crystal is stabilized by additional intermolecular N-HO hydrogen bonds.
The title compound was prepared according to a modification of the procedure of Adkins & Billica (1948). For some important properties of adamantane-bearing compounds, see: Cromwell et al. (1985), van Bommel et al. (2001).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2796 ).
The financial support of this work by the Science Foundation of Czech Republic (grant No. 203/06/P362) and by the Czech Ministry of Education (project No. MSM 7088352101) is gratefully acknowledged.
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